How far is Chester, CT from Bridgeport, CT?
The driving distance from Chester, CT to Bridgeport, CT is about 53.9 miles (86.7 km), with a travel time of about 01h 00m by car.
- The straight-line flight distance is about 41.3 miles (66.5 km).
- For a round trip, plan for roughly 02h 01m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 01h 00m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Town in New Haven County, Connecticut, United Sates
Route Weather Snapshot
Check the forecast at both ends before you head out.
Rain Showers Likely
Partly Sunny then Slight Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Chester and Bridgeport.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester and Bridgeport.
-
1
Start on Water Street
1 m · 4 sec · Water Street
-
2
Turn left onto Main Street
2620 ft · 1 min · Main Street
-
3
At the end of the road, turn right onto Middlesex Turnpike
2293 ft · 45 sec · Middlesex Turnpike
-
4
Continue on Main Street
1.2 km · 1 min · Main Street
-
5
Turn right onto Elm Street
1.9 mi · 3 min · Elm Street
-
6
Turn right onto Winthrop Road
2.4 mi · 4 min · Winthrop Road
-
7
Turn left onto Stevenstown Road
2.1 mi · 4 min · Stevenstown Road
-
8
Continue on Horse Hill Road
2.5 mi · 4 min · Horse Hill Road
-
9
Take the ramp right toward I 95 South
1164 ft · 28 sec
-
10
Merge slight left
41.2 mi · 54 min
-
11
Take the exit slight right toward Lafayette Boulevard, Harbor Yard
100 m · 8 sec
-
12
Keep slight right to continue on Downtown Bridgeport, Lafayette Boulevard
889 ft · 24 sec
-
13
Turn straight onto Lafayette Boulevard
1444 ft · 40 sec · Lafayette Boulevard
-
14
Turn straight onto Lafayette Circle
73 m · 10 sec · Lafayette Circle
-
15
Turn right onto Fairfield Avenue
1090 ft · 24 sec · Fairfield Avenue
-
16
Arrive at your destination
0 m · 1 sec · Fairfield Avenue
Car Route Details
A richer read on the saved driving route between Chester and Bridgeport.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 95 South
Merge slight left
41.2 mi · 00h 54m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Rain Showers Likely leaving Chester and Partly Sunny then Slight Chance Rain Showers near Bridgeport.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chester to Bridgeport?
The road trip is about 53.9 miles (86.7 km) and usually takes 01h 00m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Branford is a useful midpoint, sitting about 26.3 miles from Chester and 27.5 miles from Bridgeport.
How much longer is the road route than the straight-line distance?
The direct path is about 41.3 miles (66.5 km), while the road route adds roughly 12.6 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 4:28 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.50 one way or $14.99 round trip. Estimated CO2 is about 16.9 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers Likely around Chester and Partly Sunny then Slight Chance Rain Showers near Bridgeport.
Stop Ideas Near Branford
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Branford.
Union Station
Wallingford station
Meriden Transit Center
Bridgeport
Flight Path Map
This map shows the direct air route between Chester and Bridgeport. Straight-line distance: 41.35 mi (66.54 km).
#1 Chester
Town in Middlesex County, Connecticut, United States
| Population | 4,175 |
| Coordinates | 41.4031500, -72.4509200 |
| Altitude | 5 |
| Country | United States |
#2 Bridgeport
The second most populous city in Connecticut.
| Population | 143,525 |
| Coordinates | 41.1792300, -73.1894500 |
| Altitude | 1 |
| Country | United States |
End: Fairfield Avenue (-73.189437, 41.179239)
Estimated Travel Time
Distance: 87 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 47m |
| 40 mph (64.37 km/h) | 01h 20m |
| 50 mph (80.47 km/h) | 01h 04m |
| 60 mph (96.56 km/h) | 00h 53m |
| 70 mph (112.65 km/h) | 00h 46m |
| 80 mph (129 km/h) | 00h 40m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.95 | $7.50 | $14.99 |
| Mid-grade | $4.46 | $8.47 | $16.94 |
| Premium | $4.86 | $9.23 | $18.46 |
| Diesel | $6.00 | $11.39 | $22.79 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Connecticut · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.